Journal of Organic Chemistry p. 4374 - 4377 (1983)
Update date:2022-08-05
Topics:
Oku, Akira
Nozaki, Yohko
Hasegawa, Hiroshi
Nishimura, Jun
Harada, Toshiro
The Diels-Alder reaction of 6,6-dimethylfulvene with 2-acetoxyacrylonitrile gave two different adducts, 2-acetoxy-2-cyano-7,7-isopropylidenebicyclo<2.2.1>hept-5-ene (3, 70percent) and 2-acetoxy-2-cyano-1-isopropenylbicyclo<2.2.1>hept-5-ene (4, 18percent).The formation of 4, which has not been reported before, can be suppressed by adding pyridine to the reaction mixture.Hydrolysis of 3 by sodium methoxide, followed by successive treatment with unsolvated hydroxide ion, peroxyformic acid, lithium aluminum hydride, and lead tetraacetate, gave 5-(2-hydroxyethyl)-2-cyclopenten-1-one (15, 35percent from 3).
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Doi:10.1246/bcsj.56.1803
(1983)Doi:10.1016/S0040-4039(00)81866-3
(1983)Doi:10.1002/chem.200500784
(2005)Doi:10.1021/acs.joc.1c01375
(2021)Doi:10.1016/j.bmc.2005.09.009
(2006)Doi:10.1016/S0040-4039(00)81896-1
(1983)
